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📆 Itinerary: One Perfect Week on Martha's Vineyard for a First Timer
a 7-day itinerary ensuring you see all the beauty and history of MV
My itinerary for the perfect week on Martha’s Vineyard! I’ve included bucket list items, favorite restaurants, a glimpse of the beauty and history of each town…I’ve tried to construct my perfect week :)
This itinerary is weather-agnostic, so if you’re stuck with a rainy day feel free to swap out some of the items from our rainy day guide. If you click over to the itineraries section of our website, you’ll also find recommendations for: off-season, toddler and kid-friendly, dog-friendly, romantic weekends, bachelorette parties and more.
This itinerary comes with the assumption that you’re bringing your car to the island. If you choose not to, here’s a roundup of ways to get around. It also assumes you’re coming between April and November, when most places are open. If you need help planning your travel to the island, check this guide. Enjoy!
Settle In: Unpack, and settle in. Stop by a local grocery store to grab any provisions you need for your space.
Eat: Grab your inaugural hot lobster roll from Lookout Tavern, everyone’s favorite meal after getting off the ferry!
Explore: If you have some extra time, walk to Jetty Beach (Eastville) and enjoy the view, or catch some live music at The Ritz.
Oak Bluffs Day: two picnics, some walking + a nice dinner
Eat: Winston’s Kitchen - grab the linguiça, egg and cheese on a Cape Cod Bagel and have a picnic on one of the benches overlooking the harbor.
Explore: Explore the Gingerbread Houses at the MVCMA and ride the historic Flying Horses Carousel
Eat: grab a poke bowl from Tigerhawk Sandwich and pack it in your bag or bike basket
Explore: Take a walk or bike from Inkwell to State Beach from downtown Oak Bluffs. We love this walk and the opportunity to see the water and feel the ocean breeze.
Eat: Red Cat Kitchen or Sweet Life Cafe
Explore: After getting dressed up and eating local scallops or seafood for dinner, take a sunset walk around the Harbor and get a drink at Coop or Nancy’s. Pause at the fishing pier, drink a dirty banana and enjoy the nightlife.
Edgartown Day: your shopping day, a lighthouse, and a lil history
Eat: grab a fancy latte from Behind the Bookstore
Explore: Shopping in downtown Edgartown! Easily the best shopping options of the island, this is where you’ll get to grab that t-shirt from Black Dog, that hat from Vineyard Vines or your Lilly dress for tonight’s dinner.
Eat: grab a table on the top deck of the The Seafood Shanty and get that fish and chips al fresco.
Explore: After lunch, explore the The Carnegie and cap it off with a walk to Edgartown Light.
Eat: The Covington
Explore: if you’re into live music, check out Port Hunter, or if not then take a walk over to the Chappy Ferry Dock and watch the sunset.
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Vineyard Haven Day: some casual eats, history and a movie
Eat: Waterside Market
Explore: bring your book and take a little walk over to Owen Park and sit and enjoy the view of the ferries coming and going.
Eat: a casual lunch spot, you can grab whatever fried fish you were craving from Net Result
Explore: Find your way to the Martha’s Vineyard Museum and learn about the history of MV and the Wampanoag tribe.
Eat: Beach Road
Explore: MV Film Center curates incredible films and opportunities, take a look at whatever movie showing they have to offer
Up-Island Day: farm and harbor scenery, and a gorgeous overlook
Eat: eat the best croissant you can imagine at Grey Barn
Explore: follow that with a Farm Tour where you learn about the origins of the meat, cheeses and bakery at Grey Barn
Eat: Larsen’s Fish Market
Explore: after grabbing some chowder, wander around Menemsha Fishing Village where you can see boats docking and unloading from their most recent excursions.
Explore: before the meal of a lifetime, head over to explore Gay Head Light and take some photos at the Aquinnah Cliffs Overlook
Eat: Outermost Inn
Beach or Water Day: when in MV we suggest dedicating a whole day to the water - whether that be a beach day or boat tide there’s plenty of options.
Eat: grab a pizza or cheese plate from Bad Martha Brewery
Explore: watch the sunset at South Beach to cap off a great day on the water
Exploring the Farmer’s Market + Chappy
Explore: take a short trip to the West Tisbury Farmer’s Market in the morning to get some goodies. You can grab some baked goods for breakfast or provisions for the remainder of your day . If you have time, consider stopping by Alley’s General Store and Field Gallery which are also located in West Tisbury.
Explore: if you still have time in the afternoon, drive over to Edgartown, park, and bring some bikes over to Chappaquiddick for a nice bike ride. Remember that there’s no place to eat there, so bring whatever snacks you got in the morning for a little beach picnic while you watch the sunset.